The Riskiest Assumption is the one assumption in a venture that would cause the most damage if proven false — and therefore must be tested first. Every new product and business model rests on dozens of assumptions. The art lies in identifying the most critical one and focusing limited resources on it first, rather than starting with less risky hypotheses.
In practice, a simple exercise helps: the team lists all assumptions and evaluates each on two dimensions — how likely is it that the assumption is wrong, and how severe would the consequences be? The assumption with the highest combination of uncertainty and impact is tested first. An example: a team plans a platform for sustainable consumption. The riskiest assumption is not whether the platform works technically but whether the target group is willing to pay a premium for sustainable products. Testing this assumption takes priority over everything else.
The concept is closely linked to the Lean Startup methodology and disciplines teams not to lose themselves in execution before the fundamentals are clarified.